Retirement in Spoleto for a US citizen

I am an American married to an Italian living near Bologna. I cannot speak specifically about Spoleto--which is beautiful--but give you my two cents on the Italian experience. If you have the means and are retired I think you'd love it. The negative side to Italy is the work world and bureaucracy which you'd have minimal exposure to as a retiree after the initial visas and residence permits are obtained. Everything else -- the food, people and scenery -- is pretty much as advertised.

I'd go for the visa and then get your residence permit (required) once there. Citizenship takes over two years now and doesn't give you much more than residence which will be plenty of paperwork in and of itself. Everything in Italy is based on full-time residence (6 months +) whether we are talking taxes, healthcare etc. even for Italians.

I'd really work on your Italian to have a better experience. While much more English is spoken in Italy nowadays, I wouldn't count on finding many people with more than basic English. I live in a town of 7,000 people and would be hard pressed to find someone fluent.